357 Chestnut Hill Road, Woodstock, NY 12498 (MLS# 20265197)

Current Price: $595,000

Original List Price: 595000

List Price: $595,000

Status: Active

Listing Contract Date: 2026-09-08

Property Sub Type: Single Family Residence

Listing Agreement: Exclusive Right To Sell

Owner Name: Polowski Family Trust

Occupant Type: Owner

Lease Considered YN: No

Rooms Total: 4

Bedrooms Total: 2

Bathrooms Total: 1

Bathrooms Full: 1

Above Grade Finished Area: 1338

Below Grade Finished Area: 260

Living Area: 1338

New Construction YN: No

Year Built: 1970

Garage YN: Yes

Attached Garage YN: No

Garage Spaces: 1

Lot Size Acres: 1.7

Basement YN: Yes

Stories: 1

Sign On Property YN: No

List Price/SqFt: 444.69

Public Remarks: A STORYBOOK WOODSTOCK RETREAT IN THE WOODS Some homes provide shelter; others provide sanctuary. 357 Chestnut Hill Road is a sanctuary in the woods--a soulful Woodstock retreat where sunlight spills through skylights, pine glows underfoot, and the forest seems to lean in and whisper, ''stay awhile.'' Set on 1.6 wooded acres with approximately 257 feet of road frontage, this enchanting red-clad hideaway has been treasured by one close family since 1970. Follow the gravel drive beneath a leafy canopy and the home gradually reveals itself among the trees, its warm wood exterior appearing almost organically from the landscape. Secluded without feeling isolated, it captures the creative, carefree spirit that has long made Woodstock irresistible. Inside, 1,338 square feet includes a primary bedroom, a bath, a kitchen, a wonderfully versatile loft, and the home's showpiece: a spacious, cozy living room where an exposed beamed-wood ceiling creates an architectural rhythm overhead, while skylights pour pools of daylight across pine floors below. Windows frame the surrounding woodland. A characterful brick fireplace anchors it all. On crisp Catskills evenings, the hearth becomes the heart of the house--a natural gathering place for conversation, contemplation, and fireside nights. Rustic textures, warm woods, and natural light lend the room an atmosphere at once dramatic and deeply comfortable. The adjoining kitchen and dining area anchor the country cabin's soul with wood cabinetry, exposed beams, a vaulted ceiling, and an overhead skylight. Equipped with a refrigerator, range/oven, dishwasher, and washer/dryer, it is an inviting, unpretentious space for everything from pancakes at sunrise to pasta and pinot after a day exploring. And then there is the porch! Wrapping around two sides of the kitchen, the sprawling screened porch creates an irresistible indoor-outdoor area suspended within the trees. Here, the forest becomes the wallpaper and birdsong the soundtrack. Rain can patter overhead, leaves can rustle beyond the screens, and summer evenings can linger long after the sun disappears. The upper loft adds an unexpected dimension to the home's mostly single-level layout. Wrapped in warm wood, this flexible aerie can readily accommodate an additional sleeping space and a home office, library, studio, meditation area, or creative escape. Space creates possibility, and possibility gives a home room to evolve. Four split-system units add modern comfort, while a 260-square-foot partial basement provides additional utility. The house's roof was replaced in 2020. Outside, the property becomes a private woodland world. Mature trees tower overhead, sunlight dapples the forest floor, and the home's distinctive red exterior provides a warm counterpoint to the seemingly endless green. The gently winding gravel drive continues uphill to a particularly valuable feature: an oversized detached garage. With its dedicated entrance, windows, and loft storage above, the garage offers far more than parking. Think workshop, equipment storage, hobby headquarters, or simply the rare luxury of having room for all the things that make country life more enjoyable. Its roof was replaced in 2023. Yet the real luxury here cannot be quantified by acreage or square footage. It is privacy, peace, and place. For more than half a century, one family has returned to this home, lovingly cared for it, gathered within it, and called it their retreat. That continuity gives 357 Chestnut Hill Road something no renovation can manufacture: soul. The house does not ask to be something it isn't; its weathered woods, exposed beams, skylights, fireplace, loft, porch, and forest setting tell an authentic story of Woodstock country living--and invite a new owner to write its next chapter. Retreat becomes refuge; refuge becomes home; and every great story needs a place to begin--make 357 Chestnut Hill Road the beginning of yours.

Major Change Timestamp: 2026-09-08T17:16:51Z

Major Change Type: New Listing

Status Change Timestamp: 2026-09-08

Liber/Book: 7101

Page: 138

Section: 27.4

Frontage Length: 257 feet

Showing Attended YN: Yes

Basement Level: Basement

Bathroom Level: Main

Kitchen Level: Main

Living Room Level: Main

Primary Bedroom Level: Main

Other Room Level: Main

Street Number: 357

Street Name: Chestnut Hill

Street Suffix: Road

County: Ulster

State: NY

Zip Code: 12498

Town (Taxable): Woodstock